US3875201A - Dialkoxyxanthogendisulphides - Google Patents

Dialkoxyxanthogendisulphides Download PDF

Info

Publication number
US3875201A
US3875201A US305133A US30513372A US3875201A US 3875201 A US3875201 A US 3875201A US 305133 A US305133 A US 305133A US 30513372 A US30513372 A US 30513372A US 3875201 A US3875201 A US 3875201A
Authority
US
United States
Prior art keywords
weight
xanthogendisulphide
ether
parts
chloroprene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US305133A
Other languages
English (en)
Inventor
Rudolf Mayer-Mader
Jurgen Boldt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to US05/495,409 priority Critical patent/US3984384A/en
Priority to US05/495,408 priority patent/US4000222A/en
Application granted granted Critical
Publication of US3875201A publication Critical patent/US3875201A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F36/14—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
    • C08F36/16—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen containing halogen
    • C08F36/18—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen containing halogen containing chlorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F36/14—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen
    • C08F36/16—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated containing elements other than carbon and hydrogen containing halogen

Definitions

  • Dialkoxyxanthogendisulphides their production by reacting an alcohol and carbondisulphide in the presence of alkali and subsequent oxydation, use of these dialkoxyxanthogendisulphides as molecular weight regulators in polymerisation processes and a mixture of chloroprene-copolymers made in the presence of dialkoxyxanthogendisulphides.
  • This invention relates to dialkoxyxanthogendisulphides. to a process for their production andto a process for polymerising dienes in the presence of these dialkoxyxanthogendisulphides.
  • dialkoxyxanthogendisulfides according to the invention correspond to the general formula (I):
  • R-O-C-S-S-C-O-R (I) wherein the R's are equal or different and each represents wherein R is alkyl having I to l() carbon atoms;
  • R is linear or branched alkylene having 3 to 10 carbon atoms.
  • R is alkyl having 3 to l carbon atoms
  • n and n are 2. 3 or 4:
  • m are l or 2.
  • both Rs are equal.
  • dialkoxyxanthogendisulfides are preferred:
  • the invention also relates to a process for producing dialkoxyxanthogendisulphides of formula (I) wherein an alcohol ROH (R as defined above) is reacted with carbon disulphide in the presence of an alkali metal form to from the corresponding alkali xanthogenate which is then oxidised to form the corresponding xanthogcndisulphide.
  • ROH dialkoxyxanthogendisulphides of formula (I) wherein an alcohol ROH (R as defined above) is reacted with carbon disulphide in the presence of an alkali metal form to from the corresponding alkali xanthogenate which is then oxidised to form the corresponding xanthogcndisulphide.
  • suitable alcohols ROH are:
  • diethyleneglycol monomethyl ether 2. diethylene glycol monoethyl ether 3. diethylene glycol monopropyl ether 4. diethylene glcyol monoisopropyl ether 5. diethylene glcyol monobutyl ether 6. diethylene glycol monoisobutyl ether 7. diethylene glycol monopentyl ether 8. diethylene glycol monoisopentyl ether 9. diethylene glycol monohexyl ether diethylene glycol monoisohexyl ether ethylene glycol monopropyl ether 12.
  • ethylene glycol monoisopropyl ether ethylene glycol monobutyl ether ethylene glycol monoisobutyl ether ethylene glycol monopentyl ether ethylene glycol monoisopentyl ether ethylene glycol monohexyl ether ethylene glycol monoisohexyl ether
  • propylene glycol monomethyl ether isopropylene glycol monomethyl ether
  • butylene glycol monomethyl ether isobutylene glycol monomethyl ether butylene glycol monoethyl ether 3-methoxy-l-butanol 27. 1,3-glycerin diethyl ether.
  • the process is generally carried out as follows: An alcohol ROH (R as defined above) and an aqueous alkali metal hydroxide solution are mixed to about 0 to 30C so that the amounts of alcohol and of hydroxide are equimolar or approximately equimolar.
  • the aqueous alkali metal hydroxide solution is preferably 20 to percent by weight.
  • the preferred alkali hydroxides are sodium and potassium hydroxides.
  • a suitable oxidising agent in an amount of from 0.5 to 0.7 mols per mol of alkalixanthogenate, such as hydrogen peroxide or potassium pcroxy disulphate (in the form of an aqueous solution at a temperature of 10 to 40C, preferably 20C, causing formation of the corresponding xanthogendisulphide.
  • This product is water-insoluble and precipitates. It is separated from the aqueous phase (for example by filtration) and dried. The reaction taking place is illustrated in the following equation:
  • the invention also relates to a process for polymerising conjugated diolefins and for copolymerising conjugated diolefins with a-olefins in the presence of radical initiators and of dialkoxyxanthogendisulphides of formula (l) as molecular weight regulators.
  • Suitable conjugated diolefins include those having 4 to 8 carbon atoms, such as butadiene, isoprene and piperylene. Chloroprene and 2,3-dichlorobutadicnc are preferred. Acrylonitrile, styrene and ethyl acrylate are preferred a-olefins.
  • a-olefins can be copolymerised in quantities of up to 40 percent by weight, based on the diolefm.
  • suitable radical polymerisation catalysts include peroxides, azo compounds and so-called redox systems, i.c., combinations of peroxides and reducing compounds, such as: cumcne hydroperoxide, pinane hydroperoxide, potassium peroxy disulphate, tert.- butyl hydroperoxide, azo-bis-isobutyronitrile; as well as cumcne hydroperoxide, combined with formaldehyde sulphoxylate, iron salts or formamidine sulphinic acid.
  • Polymerisation is preferably carried out in aqueous emulsion, starting with an aqueous phase containing an emulsifier preferably in a quantity of from 0.1 to percent by weight.
  • suitable emulsifiers include alkali alkyl sulphonates, alkali alkyl sulphates, long-chain earboxylic acids, resinic acids and polyether alcohols.
  • the monomer or monomers is/are emulsified into the aqueous phase together with from 0.05 to percent by weight, preferably from 0.15 to 1 percent by weight, based on monomer, of a dialkoxyxanthogendisulphide of formula (1). Subsequently the radical initiator is added.
  • Polymerisation temperatures of to +100C and preferably 5 to 50C are suitable (emulsion polymerisation of chloroprene is basically known see e.g., U.S. Pat. Nos. 3,042,652, 3,147,317 and 3,147,318).
  • dialkoxyxanthogendisulphides function as molecular weight regulators; they reduce the molecular weight of the polymers obtained compared with polymers made in their absence. This is demonstrated by comparing Mooney viscosities.
  • dialkoxyxanthogendisulphides of the invention are especially molecular weight regulators in the polymerisation of chloroprene.
  • Polychloroprene obtained in their presence has particularly favourable processing properties. These are most pronounced in mixtures of uncrosslinked benzene-soluble polychloroprenes produced in accordance with the invention and crosslinked benzene-insoluble polychloroprenes. In addition to favourable processing properties, these mixtures also have particularly high strength.
  • the invention also relates to a mixture of an uncrosslinked benzene-soluble chloroprene polymer (a) and a crosslinked benzene-insoluble chloroprene polymer (b), wherein the uncrosslinked benzene-soluble chloroprene polymer is a polymer ofchloroprene and optionally up to 40 percent by weight (based on monomer mixture) of an a-olefin prepared in the presence of from 0.05 to 30 percent by weight (based on monomer) of a dialkoxyxanthogendisulphide of formula (1).
  • the benzene-soluble chloroprene polymer in this mixture is a product the preparation of which has been described above.
  • Crosslinked benzene-insoluble chloroprene polymers suitable for admixture with benzene-soluble chloroprene polymers can be obtained in latex form by various methods.
  • conventional chloroprene polymerisation can be continued to high (e.g., to percent) conversion with no or only a small quantity of a chain-transfer agent, such as an alkyl mercaptan or a dialkylxanthogendisulphide.
  • a chain-transfer agent such as an alkyl mercaptan or a dialkylxanthogendisulphide.
  • chloroprene is eopolymerised with a copolymerisable monomer containing two or more polymerisable double bonds.
  • Suitable comonomers include divinyl benzene and esters of methacrylic acid with polyhydroxy compounds, for example alkylene glycols. dihydroxy benzene or trimethylol propane, containing at least two methacrylic acid moieties.
  • crosslinked chloroprene polymers are made by the same basic process which yields benzenesolublc chloroprene polymers, the only difference being that monomer conversion is increased, for example to from 90 to 100 percent.
  • a latex of a benzene-soluble chloroprene polymer is subjected to a crosslinking post-treatment.
  • suitable post-treatments are irradiation with actinic light as described in U.S. Pat. No. 3,042,652 and treatment with an organic peroxy compound as described in U.S. Pat. No. 3,147,318.
  • the crosslinked chloroprene polymers up to about 20 percent of the chloroprene can be replaced by another conjugated diolefins or a-olefins, examples of which are given in the description relating to the preparation of the benzene-soluble chloroprene polymers.
  • diesters correspond to the general formula (11):
  • copolymers are made by the conventional aqueous emulsion polymerisation used for making polychloroprene. These eopolymers and the process for their manufacture are described in British Pat. No.
  • Mixtures of crosslinked and non-crosslinked chloroprene polymers are made. e.g. by thoroughly mixing them in latex form and subsequently recovering the solid polymer mixture. for example by low-temperature Coagulation (as described in US. Pat. No. 2.187.146) or by drying on cylinders (as described in US. Pat. No. 2,914.49? It is also possible to mix the solid polymers mechanically. for example by kneading on mixing rolls or in an internal mixer (such as a Banbury mixer or a Werner-Pfleidercr mixer).
  • the weight ratio of the benzene-soluble dialkoxyxanthogendisulphide modified chloroprene polymer (a) to the crosslinked chloroprene polymer (b) is preferably from about 2():l to I11 most preferably from 4:] to lzl.
  • the polychloroprene mixtures of the invention can be processed to form rubber mixtures and vulcanised in the same way as conventional polychloroprenes. They can be used for all purposes ofconventional polychloroprenes. Their particular advantage is improved processing compared to benzene-soluble and benzeneinsoluble polychloroprenes and improved stability under thermal stress compared with mixtures of conventional benzene-soluble and benzene-insoluble polychloroprenes.
  • EXAMPLE I The xanthogendisulphide of diethylene glycol monoethyl ether 88 g of sodium hydroxide are dissolved in 90 g of pure water in a 3-litre-flask with stirring. 268 g ofdiethylene glycol monoethyl ether are then added and the A solution of 300 g of ammonium persulphate in 2 litres of pure water is then run into the obtained reaction mixture of the xanthogenate formed. The xanthogendisulphide formed by oxidation precipitates, is filtered off. washed with pure water, and redissolved in ether. The ether solution is dried with anhydrous sodium sulphate and the ether evaporated on a rotary evaporator. The yield of xanthogendisulphide is 22] g.
  • the xanthogendisulphidc of B-methoxy-l-butanol 88 g of sodium hydroxide are dissolved in 90 g of pure water in a 3-litre flask with stirring. 208 g of 3 25 methoxy-l-butanol are then added. and the mixture stirred for a further 2 hours. After cooling to C 176 g ofcarbon disulphide are added dropwise with stirring so that the temperature does not exceed C; stirring is continued for a further 2 hours. a solution of 300 g of ammonium persulphate in 2 litres of pure water is then run into the obtained reaction mixture ofthe xanthogenate formed. The xanthogendisulphide formed by oxidation precipitates, is filtered off. washed with pure water and redissolved. The ether solution is dried with anhydrous sodium sulphate and theether evaporated on a rotary evaporator. The yield of xanthogendisulphide is 310 g.
  • EXAMPLE 2 The xanthogemlisulphide of l.3-glycerin diethyl ether l5() g of sodium hydroxide are dissolved in ISO g of pure water in a 3-litre flask with stirring. 2% g of glycerin-l .3-diethyl ether are then added and the mix- The xanthogendisulphide of propoxy ethylene glycol 88 g of sodium hydroxide are dissolved in 90 g of a pure water in a 3-litre flask with stirring. 208 g of sodium sulphate and the ether evaporated on a rotary 0 propoxy ethylene glycol are then added and stirring continued for 2 hours.
  • the temperature is increased to 43C and polymerisation initiated by an activator solution of 2.5 parts by weight of formamidine sulphinic acid in 97.5 parts by weight of pure water.
  • the activator solution is added dropwise.
  • the temperature is increased to 43C and polymerisation initiated by an activator solution of 2.5 parts by weight of formamidine sulphinic acid and 97.5 parts by weight of pure water.
  • the activator solution is added dropwise.
  • r was selected as followsf r 0.3 part by weight, and
  • the temperature is increased to 43C and polymerisation initiated by an activator solution of 2.5 parts by weight of formamidine sulphinic acid and 97.5 parts by weight ofpure water.
  • the activator solution is added dropwise.
  • the phases are separately prepared and introduced into a reaction vessel. 63 parts by weight of butadiene are then introduced under pressure.
  • the temperature is adjusted to 20C and polymerisation activated with l percent by weight, based on monomers, of potassium persulphate. At a monomer conversion of approximately 75 percent. the residual monomer is removed, the latex stabilised and the polymer precipitated from the latex with an electrolyte and subsequently dried.
  • the polymer has a Mooney viscosity ML-4/l00C of about 45. If no xanthogendisulphide is present in this polymerisation. Mooney viseosities ML-4'/l00C above 200 are found.
  • Mixture A i The polychloroprene latex of Example V 2 is mixed with the polychloroprene latex according to Example V I so that the mixture contains 85 parts by weight of the benzene-soluble polyehloroprene and parts by weight of the benzene-insoluble polyehloroprene.
  • the solid polychloroprenc mixture is recovered from the latex mixture by low-temperature coagulation, separation and drying of the solids.
  • Mixture B (for comparison) is prepared from the latices of examples V 3 and V l in exactly the same way as described in A.
  • R is linear or branched alkylene having 3 to 10 carbon atoms: R;, is alkyl having 3 to l0 carbon atoms; :1 and n are 2. 3 or 4: and m is l or 2.
  • R is -CH CH- ,OCH. ,CH OC H 3.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US305133A 1971-11-13 1972-11-09 Dialkoxyxanthogendisulphides Expired - Lifetime US3875201A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US05/495,409 US3984384A (en) 1971-11-13 1974-08-07 Process using dialkoxy-xanthogendisulphides as molecular weight regulators
US05/495,408 US4000222A (en) 1971-11-13 1974-08-07 Mixture of benzene-soluble and benzene-insoluble chloroprene polymers wherein the former polymer is prepared in the presence of a dialkoxyxanthogendisulphide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2156453A DE2156453C3 (de) 1971-11-13 1971-11-13 Dialkoxyxanthogendisulfide, Verfahren zu deren Herstellung und ihre Verwendung als Molekulargewichtsregler

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US05/495,409 Division US3984384A (en) 1971-11-13 1974-08-07 Process using dialkoxy-xanthogendisulphides as molecular weight regulators
US05/495,408 Division US4000222A (en) 1971-11-13 1974-08-07 Mixture of benzene-soluble and benzene-insoluble chloroprene polymers wherein the former polymer is prepared in the presence of a dialkoxyxanthogendisulphide

Publications (1)

Publication Number Publication Date
US3875201A true US3875201A (en) 1975-04-01

Family

ID=5825031

Family Applications (1)

Application Number Title Priority Date Filing Date
US305133A Expired - Lifetime US3875201A (en) 1971-11-13 1972-11-09 Dialkoxyxanthogendisulphides

Country Status (10)

Country Link
US (1) US3875201A (cs)
JP (2) JPS5710102B2 (cs)
BE (1) BE791228A (cs)
CA (1) CA984402A (cs)
CS (2) CS180648B2 (cs)
DE (1) DE2156453C3 (cs)
FR (1) FR2162914A5 (cs)
GB (1) GB1369349A (cs)
IT (1) IT973478B (cs)
NL (1) NL168828C (cs)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4180638A (en) * 1975-11-03 1979-12-25 Bayer Aktiengesellschaft Storable polychloroprene adhesives and a process for their production employing xanthogen disulphides
US20040110964A1 (en) * 2002-09-20 2004-06-10 Dirk Achten Dithiocarbamic esters
US20050085584A1 (en) * 2003-09-18 2005-04-21 Rudiger Musch Aqueous adhesive dispersions
US20050143498A1 (en) * 2003-04-22 2005-06-30 Rudiger Musch Aqueous adhesive dispersions
US20080028268A1 (en) * 2002-12-18 2008-01-31 Semiconductor Energy Laboratory Co., Ltd. Image display device and testing method of the same
US20090197993A1 (en) * 2006-04-06 2009-08-06 Musch Ruediger Preparations for use in concrete
US20120283351A1 (en) * 2009-09-17 2012-11-08 Lanxess Deutschland Gmbh Nitrile rubbers and production thereof in organic solvents
US9195215B2 (en) 2011-11-29 2015-11-24 Bayer Intellectual Property Gmbh Holographic medium having a protective layer
CN110036048A (zh) * 2016-12-14 2019-07-19 电化株式会社 黄原改性氯丁二烯橡胶及其橡胶组合物、以及其硫化成型体

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01141328A (ja) * 1987-11-27 1989-06-02 Hitachi Ltd 差圧伝送器
JPH0213753U (cs) * 1988-07-11 1990-01-29
EP3825375A1 (de) 2019-11-20 2021-05-26 Covestro Deutschland AG Nassverklebung von lagerstabilen 1k-sprühklebstoffen auf basis polychloropren
EP4137540A1 (de) 2021-08-16 2023-02-22 Covestro Deutschland AG Nassverklebung von lagerstabilen sprühklebstoffen auf basis polychloropren
WO2024203715A1 (ja) * 2023-03-28 2024-10-03 デンカ株式会社 クロロプレン－不飽和ニトリル共重合体ラテックス、ゴム成分、ゴム組成物、加硫成形体、及びクロロプレン－不飽和ニトリル共重合体ラテックスの製造方法
WO2024203716A1 (ja) * 2023-03-28 2024-10-03 デンカ株式会社 クロロプレン－不飽和ニトリル共重合体ラテックス、ゴム成分、ゴム組成物、加硫成形体、及びクロロプレン－不飽和ニトリル共重合体ラテックスの製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1491021A (en) * 1922-11-10 1924-04-22 Naugatuck Chem Co Process of making thiocarbonic-acid disulphide
US2375083A (en) * 1943-08-05 1945-05-01 Monsanto Chemicals Preparation of disulphides
DE1162833B (de) * 1955-10-12 1964-02-13 Huels Chemische Werke Ag Verfahren zur Herstellung von Dibutylxanthogensaeuredisulfid
CA733532A (en) * 1966-05-03 Van Den Boogaart Krijn Process for the stabilization of thioncarbomethoxy disulphide and process for the production of a stable herbicidal composition containing thioncarbomethoxy disulphide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA733532A (en) * 1966-05-03 Van Den Boogaart Krijn Process for the stabilization of thioncarbomethoxy disulphide and process for the production of a stable herbicidal composition containing thioncarbomethoxy disulphide
US1491021A (en) * 1922-11-10 1924-04-22 Naugatuck Chem Co Process of making thiocarbonic-acid disulphide
US2375083A (en) * 1943-08-05 1945-05-01 Monsanto Chemicals Preparation of disulphides
DE1162833B (de) * 1955-10-12 1964-02-13 Huels Chemische Werke Ag Verfahren zur Herstellung von Dibutylxanthogensaeuredisulfid

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4180638A (en) * 1975-11-03 1979-12-25 Bayer Aktiengesellschaft Storable polychloroprene adhesives and a process for their production employing xanthogen disulphides
US20040110964A1 (en) * 2002-09-20 2004-06-10 Dirk Achten Dithiocarbamic esters
US7825193B2 (en) 2002-09-20 2010-11-02 Lanxess Deutschland Gmbh Dithiocarbamic esters
US7169937B2 (en) 2002-09-20 2007-01-30 Bayer Aktiengesellschaft Dithiocarbamic esters
US20070078229A1 (en) * 2002-09-20 2007-04-05 Dirk Achten Dithiocarbamic esters
US20080028268A1 (en) * 2002-12-18 2008-01-31 Semiconductor Energy Laboratory Co., Ltd. Image display device and testing method of the same
US20050143498A1 (en) * 2003-04-22 2005-06-30 Rudiger Musch Aqueous adhesive dispersions
US8519047B2 (en) 2003-04-22 2013-08-27 Lanxess Deutschland Gmbh Aqueous adhesive dispersions
US20050085584A1 (en) * 2003-09-18 2005-04-21 Rudiger Musch Aqueous adhesive dispersions
US20090197993A1 (en) * 2006-04-06 2009-08-06 Musch Ruediger Preparations for use in concrete
US20120283351A1 (en) * 2009-09-17 2012-11-08 Lanxess Deutschland Gmbh Nitrile rubbers and production thereof in organic solvents
US9023914B2 (en) * 2009-09-17 2015-05-05 Lanxess Deutschland Gmbh Nitrile rubbers and production thereof in organic solvents
US9195215B2 (en) 2011-11-29 2015-11-24 Bayer Intellectual Property Gmbh Holographic medium having a protective layer
CN110036048A (zh) * 2016-12-14 2019-07-19 电化株式会社 黄原改性氯丁二烯橡胶及其橡胶组合物、以及其硫化成型体
CN110036048B (zh) * 2016-12-14 2021-08-20 电化株式会社 黄原改性氯丁二烯橡胶及其橡胶组合物、以及其硫化成型体

Also Published As

Publication number Publication date
CS180608B2 (en) 1978-01-31
JPS56106909A (en) 1981-08-25
NL168828C (nl) 1982-05-17
DE2156453B2 (de) 1981-01-22
NL168828B (nl) 1981-12-16
CS180648B2 (en) 1977-08-31
DE2156453C3 (de) 1981-12-17
JPS4857920A (cs) 1973-08-14
FR2162914A5 (cs) 1973-07-20
DE2156453A1 (de) 1973-08-16
NL7215268A (cs) 1973-05-15
JPS5710102B2 (cs) 1982-02-24
IT973478B (it) 1974-06-10
BE791228A (fr) 1973-05-10
JPS6011049B2 (ja) 1985-03-22
CA984402A (en) 1976-02-24
GB1369349A (en) 1974-10-02

Similar Documents

Publication Publication Date Title
US3875201A (en) Dialkoxyxanthogendisulphides
US2462354A (en) Organic compound polymerization process
US3498942A (en) Emulsion polymerization of unsaturated monomers utilizing alkyl sulfide terminated oligomers as emulsifiers and resulting product
US2686772A (en) N, n-ethyleneureido esters of acrylic and methacrylic acids
US3190865A (en) Chloroprene polymerization process
US2973337A (en) Process for the polymerization of unsaturated compounds, using a borazane catalyst
US3878181A (en) Emulsion polymerisation of chloroprene with diethylhydroxy-amines as inactivator
US4319014A (en) Acid stable surfactant
US3984384A (en) Process using dialkoxy-xanthogendisulphides as molecular weight regulators
US4000222A (en) Mixture of benzene-soluble and benzene-insoluble chloroprene polymers wherein the former polymer is prepared in the presence of a dialkoxyxanthogendisulphide
US3692875A (en) Elastomeric mixture of a benzene-soluble polychloroprene and a crosslinked chloroprene polymer
US2519135A (en) Polymerization process
US2796437A (en) Divinyl disulfide preparation
US3926912A (en) Polymerizing chloroprene in the presence of xanthogen disulphides with functional groups
US3954916A (en) Process employing xanthogen disulphides with functional groups to produce chloroprene polymer blends
US2391920A (en) Polymerization catalysts
US4521576A (en) Continuous polymerization of chloroprene
US2667469A (en) Vinyl esters of hydrocarbonsulfonic acids and polymers thereof
US3776874A (en) Alkyl-sulfoxide and alkyl-sulfone terminated oligomers as emulsi-fiers in emulsion polymerizations
JPS5984911A (ja) クロロプレン重合体の製造法
US4016177A (en) Xanthogen disulphides with functional groups
US3475391A (en) Hydroxylated tetrafluoroethylene/isobutylene polymers and their preparation
US4032541A (en) Xanthogen disulphides with functional groups
US3347837A (en) Process for isolating carboxylic acidbearing chloroprene polymers
US3595847A (en) Process for the production of sulphur-modified polychloroprenes